Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/34—Alcohols
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
  • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
  • A61K8/496—Triazoles or their condensed derivatives, e.g. benzotriazoles
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
  • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
  • A61K8/4966—Triazines or their condensed derivatives
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
  • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
  • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin

Definitions

• the present invention relates to novel cosmetic compositions for topical application, for photoprotecting the skin and/or the hair against the deleterious effects of ultraviolet radiation (such compositions hereinbelow more simply referred to as antisun or sunscreen compositions), and to the use of same for the cosmetic applications indicated above.
• This invention more especially relates to the aforesaid sunscreen/cosmetic compositions comprising, formulated into a cosmetically acceptable support (vehicle, diluent or carrier), admixture of (a) a benzotriazole compound first screening agent and (b) a specific bis-resorcinyltriazine compound second screening agent.
• a cosmetically acceptable support vehicle, diluent or carrier
• UV-B radiation i.e., UV-B radiation
• UV-A radiation with wavelengths of from 320 nm to 400 nm, which causes tanning of the skin, can also induce an adverse change therein, especially in the case of sensitive skin or of skin which is continually exposed to solar radiation.
• UV-A rays cause, in particular, a loss of elasticity of the skin and the appearance of wrinkles, leading to premature skin aging.
• Such irradiation promotes triggering of the erythemal reaction or amplifies this reaction in certain individuals and may even be the cause of phototoxic or photoallergic reactions. It is thus desirable to also screen out UV-A radiation.
• antisun/sunscreen compositions are quite often in the form of an emulsion of oil-in-water type (namely, a cosmetically acceptable vehicle comprising a continuous aqueous dispersing phase and a discontinuous oily dispersed phase) which contains, in various concentrations, one or more conventional lipophilic and/or hydrophilic organic screening agents which are capable of selectively absorbing harmful UV radiation.
• screening agents and their amounts are selected as a function of the desired sun protection factor (the sun protection factor (SPF) which is expressed mathematically by the ratio of the irradiation time necessary to attain the erythemogenic threshold with the UV screening agent to the time necessary to attain the erythemogenic threshold without UV screening agent).
• SPDF sun protection factor
• EP-B-0,742,003 describes antisun/cosmetic compositions having high sun protection factors; these compositions comprise a combination of two sunscreens, namely, (a) benzene-1,4-bis(3-methylidene-10-camphorsulfonic acid), optionally in partially or totally neutralized form, as a first screening agent, and (b), as a second screening agent, a benzotriazole silicone such as those described in EP-B-0,660,701.
• sunscreen/photoprotecting products are usually considered to possess insufficient water remanence.
• the present invention features novel cosmetic or dermatological, in particular antisun/sunscreen, compositions which are essentially characterized in that they comprise, formulated into a cosmetically acceptable support, (a) as a first screening agent, at least one benzotriazole compound of formula (I) below:
• A is a hydrogen atom or a divalent radical -L-W-;
• the radicals Y which may be identical or different, are each a C 1 -C 10 alkyl radical, a halogen atom, a C 1 -C 10 alkoxy radical or a sulfonic group, with the proviso that, in the latter case, two adjacent Y radicals on the same aromatic nucleus can together form an alkylidenedioxy group in which the alkylidene moiety has 1 or 2 carbon atoms; with the further proviso that the radicals Y are other than a sulfonic group when A is other than a hydrogen atom; n is 1,2, or 3; L is a divalent radical of formula (II) below:
• X is O or NH
• Z is a hydrogen atom or a C 1 -C 4 alkyl radical
• n is an integer ranging from 0 to 3, inclusive, m is 0 or 1
• p is an integer ranging from 1 to 10, inclusive
• W is a radical of formula (1), (2) or (3) below:
• radicals R which may be identical or different, are each a C 1 -C 10 alkyl, phenyl or 3,3,3-trifluoropropyl radical, at least 80%, by number, of the radicals R being methyl radicals;
• radicals B which may be identical or different, are each a radical R or the radical V having the following formula:
• radicals R 1 and R 2 which may be identical or different, are each a C 3 -C 18 alkyl radical, a C 2 -C 18 alkenyl radical, or a residue of formula —CH 2 —CH(OH)—CH 2 —OT 1 wherein T 1 is a hydrogen atom or a C 1 -C 8 alkyl radical; or (ii) the radicals R 1 and R 2 , which again may be identical or different, can also be a residue of formula (4) below:
• R 6 is a covalent bond, a linear or branched C 1 -C 4 alkyl radical, or a residue of formula —C ml H 2ml —or —C ml H 2ml —O—wherein m l is a number ranging from 1 to 4; p 1 is a number ranging from 0 to 5; the radicals R 7 , R 8 and R 9, which may be identical or different, are each a C 1 -C 18 alkyl radical, a C 1 -C 18 alkoxy radical, or a residue of formula (5) below:
• R 10 is a C 1 -C 5 alkyl radical
• a 1 is a residue having one of the following formulae (6), (7) or (8):
• R 3 is a hydrogen atom, a C 1 -C 10 alkyl radical, a radical of formula (CH 2 CHR 5 —O) n1 R 11 wherein n 1 is a number ranging from 1 to 16, R 11 is a hydrogen atom, a methyl radical, or a residue of the formula —CH 2 —CH—(OH)—CH 2 OT 1 wherein T 1 is as defined above; R 4 is a hydrogen atom; a metal cation M, a C 1 -C 5 alkyl radical, or a residue of formula —(CH 2 )m 2 —OT 1 wherein m 2 is a number ranging from 1 to 4 and T 1 is as defined above; and Q 1 is a C 1 -C 18 alkyl radical.
• the present invention also features the manufacture of cosmetic compositions for protecting the skin and/or the hair against ultraviolet radiation, in particular solar radiation.
• the present invention features a cosmetic regime/regimen for protecting the skin and/or the hair against ultraviolet radiation, in particular solar radiation, and which comprises topically applying an effective amount of a subject composition onto the skin and/or the hair.
• the subject benzotriazole compounds of formula (I) are UV-screening agents that are per se known to this art. These are described and prepared according to the syntheses indicated in U.S. Pat. Nos. 4,316,033 and 4,328,346; EP-B-0,354,145, EP-B-0,392,883 and EP-B-0,660,701 hereby expressly incorporated by reference.
• non-silicone compounds of formula (I) in which A is a hydrogen atom according to the invention particularly exemplary are:
• the alkyl radicals may be linear or branched and are selected, in particular, from among methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-amyl, isoamyl, neopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl and tert-octyl radicals.
• alkyl radicals R that are preferred according to the invention are methyl, ethyl, propyl, n-butyl, n-octyl and 2-ethylhexyl radicals. Even more preferably, the radicals R are all methyl radicals.
• silicone compounds of formula (I) in which A is a divalent radical -L-W- it is preferred to employ those in which W corresponds to formula (1), i.e., diorganosiloxanes containing a linear chain.
• linear diorganosiloxanes those more particularly preferred are the random derivatives or the derivatives well-defined in blocks having at least one, and more preferably all, of the following characteristics:
• R is an alkyl radical and even more preferably is a methyl radical
• B is an alkyl radical and even more preferably is a methyl radical
• r ranges from 0 to 15, inclusive; s ranges from 1 to 5, inclusive;
• n is other than zero and preferably is equal to 1, and Y is then selected from among methyl, tert-butyl and C 1 -C 4 alkoxy;
• Z is a hydrogen atom or a methyl radical
• p is equal to 1.
• the bonding of the divalent radical —(X) m —(CH 2 ) p —CH(Z)—CH 2 —to the benzotriazole structural unit, which thus links said benzotriazole unit to the silicon atom of the silicone backbone, can, according to the present invention, be at any of the available positions presented by the two aromatic nuclei of the benzotriazole:
• this attachment is at position 3-, 4-, 5-(aromatic nucleus bearing the hydroxyl function) or 4′-(benzene nucleus adjacent to the triazole ring), and even more preferably at position 3-, 4- or 5-.
• the attachment is at position 3-.
• the attachment of the substituent Y can be at any of the other positions available on the benzotriazole. However, this attachment preferably is at position 3-, 4-, 4′-, 5- and/or 6-. In one preferred embodiment of the invention, the attachment is at position 5-.
• the benzotriazole silicone has the structural formula (I′) in which:
• the benzotriazole silicone has the structural formula (I′) in which:
• the benzotriazole compounds of formula (I) are advantageously present in amounts of from 0.1% to 15% and preferably from 0.2% to 10% by weight, relative to the total weight of the composition.
• the alkyl radicals are linear or branched and are selected, for example, from among methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, amyl, isoamyl, tert-amyl, heptyl, octyl, isooctyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl and octadecyl radicals;
• the alkenyl radicals are selected, for example, from among allyl, methylallyl, isopropenyl, 2-butenyl, 3-butenyl, isobutenyl, n-penta-2,4-dienyl, 3-methylbut-2-enyl, n-oct-2-enyl, n-dodec-2-enyl, isododecenyl and n-octadec-4-enyl radicals;
• the alkoxy radicals are linear or branched and are selected, for example, from among methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, amyloxy, isoamyloxy and tert-amyloxy radicals;
• the C 1 -C 5 mono- or dialkylamino radicals are selected, for example, from among methylamino, ethylamino, propylamino, n-butylamino, sec-butylamino, tert-butylamino, pentylamino, dimethylamino, diethylamino, dibutylamino and methylethylamino radicals;
• the metal cations are preferably alkali metal or alkaline earth metal cations or metallic cations selected, for example, from among lithium, potassium, sodium, calcium, magnesium, copper and zinc cations.
• the bis-resorcinyltriazine compounds of formula (III) of the invention are UV-screening agents that are also per se known to this art. These are described and prepared according to the syntheses indicated in EP-A-0,775,698 hereby expressly incorporated by reference.
• Exemplary compounds of formula (III) include:
• the compounds derived from bis-resorcinyltriazine that are more particularly preferred according to the invention are selected from the group consisting of:
• the sunscreen(s) of the bis-resorcinyltriazine compound type of formula (III) are advantageously present in the compositions according to the invention at a concentration of from 0.1% to 15% and preferably from 0.2% to 10% by weight relative to the total weight of the composition.
• the two types of sunscreen should both be present in the final composition in a respective proportion such that a synergistic effect on the water remanence imparted by the resulting combination is obtained in an appreciable, substantial and significant manner.
• concentrations and ratios of benzotriazole compounds of formula (I) and of bis-resorcinyltriazine compounds of formula (III) as described above are selected such that the sun protection factor of the final composition is preferably at least 2.
• the cosmetically acceptable support in which the various types of screening agent are formulated is an emulsion of oil-in-water type.
• the antisun/sunscreen cosmetic compositions according to the invention can contain one or more additional hydrophilic or lipophilic UVA-active and/or UVB-active sunscreen(s) (absorbers) other than the subject two screening agents.
• additional screening agents are advantageously selected, in particular, from among cinnamic derivatives; salicylic derivatives; camphor derivatives; triazine derivatives other than those described above, such as those described in EP-863,145, EP-517,104, EP-570,838 and EP-796,851; benzophenone derivatives; dibenzoylmethane derivatives; ⁇ , ⁇ ′-diphenylacrylate derivatives, benzimidazole derivatives; p-aminobenzoic acid derivatives; screening polymers and screening silicones, such as those described in WO-93/04665.
• UV-A-active and/or UV-B-active sunscreens include:
• compositions according to the invention may also contain agents for the artificial tanning and/or browning of the skin (self-tanning agents) such as, for example, dihydroxyacetone (DHA).
• self-tanning agents such as, for example, dihydroxyacetone (DHA).
• the cosmetic compositions according to the invention may also contain pigments or nanopigments (average size of the primary particles: generally ranging from 5 nm to 100 nm, preferably from 10 nm to 50 nm) of coated or uncoated metal oxides, for example nanopigments of titanium dioxide (amorphous or crystallized in rutile and/or anatase form), of iron oxide, of zinc oxide, of zirconium oxide or of cerium oxide which are all UV-photoprotective agents that are well known to this art.
• Conventional coating agents include, moreover, alumina and/or aluminum stearate.
• Such coated or uncoated metal oxide nanopigments are described, in particular, in EP-A-0,518,772 and EP-A-0,518,773.
• compositions of the invention may also comprise conventional cosmetic additives and adjuvants selected, in particular, from among fatty substances, organic solvents, thickeners, softeners, antioxidants, opacifying agents, stabilizers, emollients, hydroxy acids, anti-foaming agents, moisturizers, vitamins, fragrances, preservatives, surfactants, fillers, sequestering agents, polymers, propellants, basifying or acidifying agents, dyes, colorants, or any other ingredient usually formulated into cosmetics, in particular for the manufacture of antisun/sunscreen compositions in the form of emulsions.
• conventional cosmetic additives and adjuvants selected, in particular, from among fatty substances, organic solvents, thickeners, softeners, antioxidants, opacifying agents, stabilizers, emollients, hydroxy acids, anti-foaming agents, moisturizers, vitamins, fragrances, preservatives, surfactants, fillers, sequestering agents, polymers, propellants
• the fatty substances may be an oil or a wax or mixtures thereof, and may also be fatty acids, fatty alcohols and fatty acid esters.
• the oils may be animal, plant, mineral or synthetic oils and, in particular, liquid petrolatum, liquid paraffin, volatile or non-volatile silicone oils, isoparaffins, poly- ⁇ -olefins, fluoro oils and perfluoro oils.
• the waxes may be animal, fossil, plant, mineral or synthetic waxes that are per se known to this art.
• organic solvents exemplary are the lower alcohols and polyols.
• the thickeners may be selected, in particular, from among crosslinked acrylic acid homopolymers and modified or unmodified guar gums and celluloses such as hydroxypropyl guar gum, methylhydroxyethylcellulose, hydroxypropylmethylcellulose or hydroxyethylcellulose.
• compositions of the invention may be prepared according to techniques which are well known to this art, in particular those for formulating emulsions of oil-in-water or water-in-oil type.
• compositions may be, in particular, in simple or complex emulsion form (O/W, W/O, O/W/O or W/O/W), such as a cream, a milk, a lotion, an ointment, a gel or a cream-gel, a powder or a solid stick and may optionally be packaged as an aerosol and may be in the form of a foam or a spray.
• simple or complex emulsion form O/W, W/O, O/W/O or W/O/W
• the aqueous phase thereof may comprise a nonionic vesicular dispersion prepared according to known processes (Bangham, Standish and Watkins, J. Mol. Biol., 13 238 (1965), FR-2,315,991 and FR-2,416,008).
• the cosmetic compositions of the invention may be for protecting the human skin or the hair against ultraviolet rays, as an antisun/sunscreen composition or as a makeup product.
• the cosmetic compositions according to the invention are for protecting the human epidermis against UV rays or as an antisun/sunscreen composition
• same may be in the form of a suspension or dispersion in solvents or in fatty substances, in the form of a nonionic vesicular dispersion or, alternatively, in the form of an emulsion, preferably of oil-in-water type, such as a cream or a milk, or in the form of an ointment, a gel, a cream-gel, a powder, a solid tube, a stick, an aerosol foam or a spray.
• the cosmetic compositions according to the invention are to protect the hair, it may be in the form of a shampoo, a lotion, a gel, an emulsion or a nonionic vesicular dispersion and may constitute, for example, a rinse-out composition to be applied before or after shampooing, before or after dyeing or bleaching, before, during or after permanent-waving or straightening of the hair, a styling or treating lotion or gel, a blow-drying or hair-setting lotion or gel or a composition for permanent-waving, straightening, dyeing or bleaching the hair.
• a rinse-out composition to be applied before or after shampooing, before or after dyeing or bleaching, before, during or after permanent-waving or straightening of the hair
• a styling or treating lotion or gel a blow-drying or hair-setting lotion or gel or a composition for permanent-waving, straightening, dyeing or bleaching the hair.
• composition when used as a makeup product for the eyelashes, the eyebrows or the skin, such as a treatment cream for the epidermis, a foundation, a lipstick, an eyeshadow, a blusher, a mascara or an eyeliner, it may be in anhydrous or aqueous, solid or pasty form, for example oil-in-water or water-in-oil emulsions, nonionic vesicular dispersions or suspensions.
• the aqueous phase in particular comprising the hydrophilic screening agents
• the oily phase in particular comprising the lipophilic screening agents
• the (co)emulsifying agent(s) from 0.5% to 20% by weight, preferably from 2% to 10% by weight, also relative to the total weight of the formulation.
• the present invention also features a cosmetic regime or regimen for the skin or the hair to protect the skin/hair against the damaging effects of UV irradiation, which comprises topically applying an effective amount of a cosmetic composition as described above onto the skin or the hair.

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• Health & Medical Sciences (AREA)
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• Veterinary Medicine (AREA)
• Birds (AREA)
• Epidemiology (AREA)
• Dermatology (AREA)
• Emergency Medicine (AREA)
• Cosmetics (AREA)

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• 1999
  • 1999-02-12 FR FR9901729A patent/FR2789579B1/fr not_active Expired - Lifetime
• 2000
  • 2000-02-03 BR BRPI0009860-4A patent/BR0009860B1/pt active IP Right Grant
  • 2000-02-03 AU AU23023/00A patent/AU755972B2/en not_active Ceased
  • 2000-02-03 RU RU2001124916/14A patent/RU2211691C2/ru active
  • 2000-02-03 DE DE60016173T patent/DE60016173T2/de not_active Expired - Lifetime
  • 2000-02-03 CA CA002360207A patent/CA2360207A1/fr not_active Abandoned
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  • 2000-02-03 EP EP00901711A patent/EP1150649B1/de not_active Expired - Lifetime
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• 2006
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